This invention relates to novel herbicidal sulfonamide compounds with substituents in both positions ortho to the sulfonylurea bridge, suitable agricultural compositions thereof and a method for their use as preemergent or postemergent herbicides or plant growth regulants.
Herbicidal sulfonamides of the type described herein are generally referred to in the art as "sulfonylurea" herbicides.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. This class of herbicides, generally consists of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings. See, for example, the compounds disclosed in U.S. Pat. Nos. 4,169,719, 4,127,405, 4,120,691, 4,221,585, 4,190,432, 4,225,337, 4,371,391, 4,339,266, 4,191,553, 4,305,884, 4,214,890, 4,339,267, 4,302,241, 4,342,587, 4,310,346, 4,293,330, 4,301,286, 4,370,479 4,370,480, 4,368,067, 4,369,320, 4,348,219, 4,348,220, 4,333,760, 4,368,069, and 3,323,611 as well as European Patent Application No. 79300982.0 (Publication No. 7.687, published Feb. 6, 1980).
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of undesired vegetation to permit the growth of useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such useful crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
EPO Pub. No. 7,687, discloses herbicidal sulfonylureas bearing ortho-carboxylic acid ester groups.
EPO Pub. No. 23,141, discloses herbicidal sulfonylureas bearing ortho-sulfamoyl groups.
EPO Pub. No. 44,211, discloses herbicidal sulfonylureas bearing ortho-phenyl groups.
EPO Pub. No. 44,209, discloses herbicidal sulfonylureas bearing --CH.sub.2 OR and CH.sub.2 CO.sub.2 R.sub.8 ortho-groups.
EPO Pub. No. 35,893, discloses herbicidal sulfonylureas bearing an ortho-sulfonyl group.
EPO Pub. No. 44,212, discloses herbicidal sulfonylureas bearing ortho-sulfonate groups.
U.S. Pat. No. 4,369,058, issued Jan. 18, 1983 discloses herbicidal sulfonylureas bearing ortho-amino substituents.
EPO Pub. No. 83,975, discloses herbicidal sulfonylureas bearing ortho-heterocyclic substituents.
EPO Pub. No. 85,476, discloses herbicidal sulfonylureas bearing ortho-pyridyl, pyrimidyl, triazinyl and furanyl groups.
South African Patent Application No. 83/0127 discloses herbicidal N-arylsulfonyl-N'-pyrimidinylureas of formula ##STR1## where X is optionally substituted phenyl or naphthyl.
South African Patent Application No. 83/0441 discloses herbicidal ureas of formula ##STR2## where X is O, S, SO or SO.sub.2 ;
m is 0 or 1; and PA1 Q is any of a wide variety of moieties. PA1 R.sub.1 is H, halo, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkythio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 alkoxyalkoxy. PA1 R.sub.4 is H or CH.sub.3 ; PA1 R.sub.5 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.6 and R.sub.7 are independently CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.8 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sub.9 is CH.sub.3 or OCH.sub.3 ; PA1 R.sub.10 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.11 is H, Cl, Br, F, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.12 is H or CH.sub.3 ; PA1 R.sub.13 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA1 R.sub.14 is C.sub.1 -C.sub.3 alkyl or CF.sub.2 H; PA1 n is 0, 1 or 2; PA1 m is 0 or 1; ##STR7## W is O, S or NR.sub.18 ; W' is O or S; PA1 R.sub.15, R.sub.16, R.sub.17 and R.sub.18 are independently H or CH.sub.3 ; PA1 Q is also ##STR8## R.sub.19, R.sub.20, R.sub.22, R.sub.24 and R.sub.25 are independently H or CH.sub.3 ; PA1 R.sub.21 and R.sub.23 are independently H, CH.sub.3 or OCH.sub.3 ; PA1 Q is also ##STR9## R.sub.26, R.sub.27, R.sub.28 R.sub.29, R.sub.30 and R.sub.31 are independently H or CH.sub.3 ; ##STR10## Z is CH or N; L is O or CH.sub.2 ; PA1 X is CH.sub.3, OCH.sub.3, Cl, OCH.sub.2 CH.sub.3, OCF.sub.2 H or F; PA1 Y is H, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.3, CH.sub.2 CH.sub.3, CF.sub.3, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, O(C.sub.1 -C.sub.3 alkyl), SCH.sub.3, O(C.sub.3 -C.sub.4 alkenyl), O(C.sub.3 -C.sub.4 alkynyl), OCH.sub.2 CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CH.sub.2 Cl, OCH.sub.2 CH.sub.2 Br or OCF.sub.2 H; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, Cl or OCF.sub.2 H; PA1 Y.sub.1 is CH.sub.3 or OCH.sub.3 ; PA1 X.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; and PA1 Y.sub.3 is H or CH.sub.3 ; PA1 (a) when either one of R.sub.1 or R.sub.2 is CF.sub.3, then the other is also CF.sub.3 ; PA1 (b) R.sub.1 and R.sub.2 are not simultaneously CO.sub.2 R.sub.8 ; PA1 (c) when either one of R.sub.1 or R.sub.2 is SO.sub.2 NR.sub.9 R.sub.10, then the other must not be S(O).sub.n R.sub.5, S(O).sub.m R.sub.5, CH.sub.2 OR.sub.14 or NR.sub.6 R.sub.7 ; PA1 (d) when R.sub.9 is OCH.sub.3, then R.sub.10 is CH.sub.3 ; PA1 (e) when either one of R.sub.1 or R.sub.2 is CO.sub.2 R.sub.8, then the other must not be S(O).sub.n R.sub.5, S(O).sub.m R.sub.5 or NR.sub.6 R.sub.7 ; PA1 (f) the total number of carbon atoms in R.sub.26 to R.sub.31 combined, is equal to or less than four; PA1 (g) when X is Cl or F, then Z is CH and Y is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA1 (h) when R.sub.1 is CO.sub.2 R.sub.8 and R.sub.2 is OSO.sub.2 R.sub.13, then A is not A-1; and PA1 (i) when X or Y is OCF.sub.2 H and A is A-1, then R.sub.2 is Q. PA1 (1) Compounds of Formula 1 where A is A-1; R.sub.1 and R.sub.2 are not simultaneously Q and R.sub.4 is H. PA1 (2) Compounds of Preferred 1 where Y is CH.sub.3, CF.sub.3, CH.sub.2 OCH.sub.3, OCH.sub.3, OCH.sub.2 CF.sub.3 or OCF.sub.2 H. PA1 (3) Compounds of Preferred 2 where R.sub.3 is in either the 3- or 5-position. PA1 (4) Compounds of Preferred 3 where R.sub.1 and R.sub.2 are not simultaneously SO.sub.2 NR.sub.9 R.sub.10 or NR.sub.6 R.sub.7. PA1 (5) Compounds of Preferred 4 where R.sub.3 is H; and at least one of R.sub.1 or R.sub.2 is S(O).sub.n R.sub.5, S(O).sub.m R.sub.5, CF.sub.3, NR.sub.6 R.sub.7, SO.sub.2 NR.sub.9 R.sub.10, ##STR11## OSO.sub.2 R.sub.13 or CH.sub.2 OR.sub.14. (6) Compounds of Preferred 5 where R.sub.5 is CH.sub.3 or CH.sub.2 CH.sub.3 ; R.sub.6 and R.sub.7 are both CH.sub.3 ; R.sub.10 is CH.sub.3 ; R.sub.11 is H; R.sub.13 is CH.sub.3 or CH.sub.2 CH.sub.3 ; and R.sub.14 is CH.sub.3. PA1 (7) Compounds of Preferred 6 where X is CH.sub.3, OCH.sub.3 or Cl and Y is CH.sub.3, OCH.sub.3 or CH.sub.2 OCH.sub.3. PA1 R.sub.3 =H, Cl, F, Br, CH.sub.3, OCH.sub.3 or CF.sub.3 ; and PA1 R.sub.4 is H. PA1 R.sub.3 is as described in Equation 1; and PA1 R.sub.4 is H or CH.sub.3. PA1 R.sub.1 or R.sub.2 may also be CO.sub.2 R.sub.8, ##STR17## and OSO.sub.2 R.sub.13. PA1 R.sub.2 is C.sub.6 H.sub.4 R.sub.11 or Q. ##STR26## where R.sub.1 is SR.sub.5, CF.sub.3, NR.sub.6 R.sub.7, CO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 NR.sub.9 R.sub.10, C.sub.6 H.sub.4 R.sub.11, OH, CH.sub.2 OH, Q or ##STR27## R.sub.2 is SR.sub.5, CO.sub.2 H, CO.sub.2 R.sub.8 or CH.sub.2 OH; and R.sub.3 is as defined in Equation 2. PA1 D. W. Slocum and C. A. Jennings J. Org. Chem., 41, 3653 (1976); PA1 A. I. Meyers and K. Lutomski J. Org. Chem., 44, 4464 (1979); PA1 P. Beak and R. A. Brown J. Org. Chem., 47, 34 (1982); and PA1 P. Beak and V. Snieckus Acc. Chem. Res., 15, 306 (1982). PA1 R.sub.12 is H or CH.sub.3 ; and PA1 R.sub.8 is H, CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CH.sub.2 CH.sub.3. PA1 R.sub.3 is as defined in Equation 2. ##STR33## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above. PA1 R.sub.13 is C.sub.1 -C.sub.3 alkyl or CF.sub.3. ##STR37## wherein R.sub.3 and R.sub.13 are as defined above. ##STR38## wherein R.sub.3 and R.sub.13 are as defined above. PA1 R.sub.4 is H.
South African Patent Application No. 83/8416 discloses herbicidal sulfonamides of formula ##STR3## where A is an unsaturated or only partially saturated 5- or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms and which may be substituted; and